ArticleJournal of the American Chemical Society2020
Highly Diastereoselective Functionalization of Piperidines by Photoredox-Catalyzed α-Amino C-H Arylation and Epimerization.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed, 82 citations in OpenAlex.
- Late-stage N-Me selective alkenylation and alkynylation of drugs and unactivated tertiary amines using photoredox catalysis.Nature communications · 2026Article
- Cooperative Brønsted Acid and Photo-Promoted Stereoselective Synthesis of Substituted Piperidones.Angewandte Chemie (International ed. in English) · 2025Article
- A Charge Transfer Mediated Sequential Triplet Energy Transfer Model Beyond the Dexter Limit in Organic Photocatalysis.JACS Au · 2025Article
- Regiodivergent α- and β-Functionalization of SaturatedJournal of the American Chemical Society · 2025Article
- Photocatalytic Hydrogenation of Quinolines to Form 1,2,3,4-Tetrahdyroquinolines Using Water as the Hydrogen Atom Donor.Angewandte Chemie (International ed. in English) · 2025Article
- Switchable Enantio- and Diastereoselective Michael Additions of β-Keto Amides to Nitroolefins: Crystallization-Based Inversion of Kinetic Stereocontrol.Organic letters · 2024Article
- C-H, N-H, and O-H Bond Activations to Prepare Phosphorescent Hydride-Iridium(III)-Phosphine Emitters with Photocatalytic Achievement in C-C Coupling Reactions.Inorganic chemistry · 2024Article
- Radical Cross Coupling and Enantioselective Protonation through Asymmetric Photoredox Catalysis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Visible-Light-Mediated, Diastereoselective Epimerization of Exocyclic Amines.Organic letters · 2023Article
- Article
- Photoredox-catalyzed diastereoselective dearomative prenylation and reverse-prenylation of electron-deficient indole derivatives.Nature communications · 2023Article
- Isotopic Fractionation as a Mechanistic Probe in Light-Driven C-H Bond Exchange Reactions.Journal of the American Chemical Society · 2023Article
- Enantio- and Diastereoselective Mannich Reactions of ß-Dicarbonyls by Second Stage Diastereoconvergent Crystallization.ACS catalysis · 2023Article
- Stereochemical editing logic powered by the epimerization of unactivated tertiary stereocenters.Science (New York, N.Y.) · 2022Article
- Visible Light-Mediated, Diastereoselective Epimerization of Morpholines and Piperazines to More Stable Isomers.ACS catalysis · 2022Article
- Regioselective α-Cyanation of Unprotected Alicyclic Amines.Organic letters · 2022Article
- Visible Light-Mediated, Highly Diastereoselective Epimerization of Lactams from the Most Accessible to the More Stable Stereoisomer.ACS catalysis · 2022Article
- Synthesis of Polycyclic Isoindolines via α-C-H/N-H Annulation of Alicyclic Amines.Organic letters · 2022Article
- Photoredox-Catalyzed C-H Functionalization Reactions.Chemical reviews · 2022Review
- A Change from Kinetic to Thermodynamic Control EnablesJournal of the American Chemical Society · 2022Article
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
Abstract
We report a photoredox-catalyzed α-amino C-H arylation reaction of highly substituted piperidine derivatives with electron-deficient cyano(hetero)arenes. The scope and limitations of the reaction were explored, with piperidines bearing multiple substitution patterns providing the arylated products in good yields and with high diastereoselectivity. To probe the mechanism of the overall transformation, optical and fluorescent spectroscopic methods were used to investigate the reaction. By employing flash-quench transient absorption spectroscopy, we were able to observe electron transfer processes associated with radical formation beyond the initial excited-state Ir(ppy)
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.